sinefungin (CHEBI:45453)

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CHEBI:45453 - sinefungin

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ChEBI Name	sinefungin

ChEBI ID	CHEBI:45453

Definition	An adenosine that is the the δ-(5'-adenosyl) derivative of ornithine.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	eMolecules:636962, ZINC000100044649

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

Marvin 02121315483D

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Time for openFile(

Marvin 02121315483D

50 52 0 0 0 0 999 V2000

0.4810 -0.7620 -6.6930 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.7930 -0.5840 -5.9850 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.7520 0.1800 -6.8610 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.3310 0.9830 -7.6600 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.0730 -0.0310 -6.7540 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.5540 0.1940 -4.6900 C 0 0 0 0 0 0 0 0 0 0 0 0

0.4180 -0.5820 -3.8010 C 0 0 0 0 0 0 0 0 0 0 0 0

0.6580 0.1960 -2.5050 C 0 0 2 0 0 0 0 0 0 0 0 0

1.2290 1.5120 -2.8240 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.2200 -0.0640 2.5930 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.2660 -0.8320 2.1750 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.1390 -0.9550 3.1320 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.7110 -0.2750 4.2220 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.2210 -0.0550 5.5130 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.4330 -0.6010 5.8980 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.5120 0.6870 6.3560 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.3540 1.2110 5.9980 C 0 0 0 0 0 0 0 0 0 0 0 0

0.1620 1.0320 4.8010 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.4720 0.2990 3.8920 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.2170 -1.5600 -5.7490 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.6880 0.4590 -7.3160 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.2870 0.3270 -1.9800 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.3560 -1.2740 1.1930 H 0 0 0 0 0 0 0 0 0 0 0 0

0.1890 1.8090 6.7150 H 0 0 0 0 0 0 0 0 0 0 0 0

1.6310 -0.5800 -1.6160 C 0 0 0 0 0 0 0 0 0 0 0 0

1.8710 0.1980 -0.3210 C 0 0 1 0 0 0 0 0 0 0 0 0

0.6350 0.3420 0.3970 O 0 0 0 0 0 0 0 0 0 0 0 0

2.8440 -0.5790 0.5850 C 0 0 1 0 0 0 0 0 0 0 0 0

4.0190 0.1910 0.8470 O 0 0 0 0 0 0 0 0 0 0 0 0

2.0410 -0.8060 1.8920 C 0 0 1 0 0 0 0 0 0 0 0 0

2.8710 -0.6160 3.0390 O 0 0 0 0 0 0 0 0 0 0 0 0

0.9580 0.2990 1.8040 C 0 0 2 0 0 0 0 0 0 0 0 0

1.1210 -1.1830 -6.0360 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8340 0.1620 -6.8900 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5000 0.3250 -4.1650 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1300 1.1700 -4.9260 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3650 -0.7140 -4.3260 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0040 -1.5580 -3.5650 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0980 1.3410 -3.3060 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6070 1.9440 -3.4900 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2080 -1.5560 -1.3800 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5770 -0.7110 -2.1410 H 0 0 0 0 0 0 0 0 0 0 0 0

2.2830 1.1810 -0.5500 H 0 0 0 0 0 0 0 0 0 0 0 0

3.1090 -1.5330 0.1290 H 0 0 0 0 0 0 0 0 0 0 0 0

4.5580 -0.3210 1.4640 H 0 0 0 0 0 0 0 0 0 0 0 0

1.5860 -1.7960 1.9040 H 0 0 0 0 0 0 0 0 0 0 0 0

3.5210 -1.3320 3.0360 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3590 1.2570 2.1350 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.7750 -0.4420 6.7910 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.9420 -1.1420 5.2730 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 33 1 0 0 0 0

1 34 1 0 0 0 0

2 3 1 0 0 0 0

2 6 1 0 0 0 0

2 20 1 0 0 0 0

3 4 2 0 0 0 0

3 5 1 0 0 0 0

5 21 1 0 0 0 0

6 7 1 0 0 0 0

6 35 1 0 0 0 0

6 36 1 0 0 0 0

7 8 1 0 0 0 0

7 37 1 0 0 0 0

7 38 1 0 0 0 0

8 9 1 0 0 0 0

8 22 1 0 0 0 0

8 25 1 0 0 0 0

9 39 1 0 0 0 0

9 40 1 0 0 0 0

10 11 4 0 0 0 0

10 19 4 0 0 0 0

11 12 4 0 0 0 0

11 23 1 0 0 0 0

12 13 4 0 0 0 0

13 14 4 0 0 0 0

13 19 4 0 0 0 0

14 15 1 0 0 0 0

14 16 4 0 0 0 0

15 49 1 0 0 0 0

15 50 1 0 0 0 0

16 17 4 0 0 0 0

17 18 4 0 0 0 0

17 24 1 0 0 0 0

18 19 4 0 0 0 0

25 26 1 0 0 0 0

25 41 1 0 0 0 0

25 42 1 0 0 0 0

26 27 1 0 0 0 0

26 28 1 0 0 0 0

26 43 1 0 0 0 0

27 32 1 0 0 0 0

28 29 1 0 0 0 0

28 30 1 0 0 0 0

28 44 1 0 0 0 0

29 45 1 0 0 0 0

30 31 1 0 0 0 0

30 32 1 0 0 0 0

30 46 1 0 0 0 0

31 47 1 0 0 0 0

32 10 1 0 0 0 0

32 48 1 0 0 0 0

M END): 19 ms

reading 50 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

50 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Formula

C15H23N7O5

Net Charge

Average Mass

381.38700

Monoisotopic Mass

381.17607

InChI

InChI=1S/C15H23N7O5/c16-6(1-2-7(17)15(25)26)3-8-10(23)11(24)14(27-8)22-5-21-9-12(18)19-4-20-13(9)22/h4-8,10-11,14,23-24H,1-3,16-17H2,(H,25,26)(H2,18,19,20)/t6-,7-,8+,10+,11+,14+/m0/s1

InChIKey

LMXOHSDXUQEUSF-YECHIGJVSA-N

SMILES

N[C@@H](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1cnc2c(N)ncnc12

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	sinefungin (CHEBI:45453) has functional parent L-ornithine (CHEBI:15729) sinefungin (CHEBI:45453) has role antifungal agent (CHEBI:35718) sinefungin (CHEBI:45453) has role antimicrobial agent (CHEBI:33281) sinefungin (CHEBI:45453) is a adenosines (CHEBI:22260) sinefungin (CHEBI:45453) is a non-proteinogenic α-amino acid (CHEBI:83925)

IUPAC Name

(5S)-5-amino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]-L-norleucine

INNs	Sources
sinefungin	KEGG DRUG
sinefungina	ChemIDplus
sinefungine	ChemIDplus
sinefunginum	ChemIDplus

Synonyms	Sources
(2S,5S)-2,5-diamino-6-[(2R,3S,R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]hexanoic acid	PDBeChem
6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-beta-D-ribo-decofuranuronic acid	ChemIDplus
6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxydecofuranuronic acid	ChemIDplus
A 9145	ChemIDplus
ADENOSYL-ORNITHINE	PDBeChem
Antibiotic A 9145	ChemIDplus

Manual Xrefs	Databases
D05846	KEGG DRUG
SFG	PDBeChem
SINEFUNGIN	MetaCyc
US3758681	Patent
US5872104	Patent
View more database links

Registry Numbers	Types	Sources
3574678	Reaxys Registry Number	Reaxys
58944-73-3	CAS Registry Number	ChemIDplus
58944-73-3	CAS Registry Number	KEGG DRUG

Citations	Types	Sources
20347768	PubMed citation	Europe PMC
20859291	PubMed citation	Europe PMC
21738746	PubMed citation	Europe PMC
21781040	PubMed citation	Europe PMC
22342622	PubMed citation	Europe PMC
22362751	PubMed citation	Europe PMC
22965231	PubMed citation	Europe PMC

Last Modified

26 March 2015

CHEBI:45453 - sinefungin

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